Cyclic nitro compounds, such as ABDNAZ, are being investigated for their potential use in treating cancer. Methods of synthesizing ABDNAZ have been described, such as in U.S. Pat. No. 7,507,842 to Bednarski et al. (“Bednarski”). In Bednarski, ABDNAZ is synthesized by reacting 1-tert-butyl-3,3-dinitroazetidine (DNAZ) with bromoacetyl bromide in the presence of boron trifluoride etherate. For every mole of ABDNAZ produced, a mole of a hydrogen bromide salt of DNAZ (DNAZ HBr) is also produced as a coproduct. The ABDNAZ is isolated from the DNAZ HBr by cooling the reaction mixture, adding dichloromethane, and filtering the DNAZ HBr. Solid DNAZ HBr is sensitive to impact, friction, and other external stimuli and, therefore, must be handled carefully. The dichloromethane filtrate is washed with water, dried, and then the dichloromethane is evaporated, producing a crude ABDNAZ mixture. The product is washed sequentially with diethyl ether and dried under vacuum, yielding ABDNAZ that is approximately 98% pure and at a yield of approximately 75% (based on bromoacetyl bromide). The 2% of impurities remaining in the ABDNAZ are believed to include bromoacetic acid, unreacted DNAZ, and DNAZ HBr. This method of producing ABDNAZ is referred to herein as the Bednarski process. While the Bednarski process provides ABDNAZ at a reasonable purity and yield, the purity does not meet current industry standards for pharmaceutical uses. In addition, solid DNAZ HBr produced during the Bednarski process is an explosive compound, which adds to the complexity of producing ABDNAZ.
It would be desirable to synthesize and isolate ABDNAZ by a process that minimizes or reduces hazards associated with handling explosive intermediates, such as DNAZ HBr. The resulting ABDNAZ would have a comparable or higher yield and purity relative to that produced by the Bednarski process.